Ethyl isocyanate → HCID 68837068, compound

HRID 2112967Notes

Reaction equation

HRID 2112967 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[N:12]3[N:13]=[C:14]([NH2:16])[N:15]=[C:11]3[CH:10]=[C:9]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=2)=[CH:5][N:6]=1.[CH2:23]([N:25]=[C:26]=[O:27])[CH3:24]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C1COCC1.C1(C)C=CC=CC=1>[CH2:23]([NH:25][C:26]([NH:16][C:14]1[N:15]=[C:11]2[CH:10]=[C:9]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=[C:7]([C:4]3[O:3][C:2]([CH3:1])=[N:6][CH:5]=3)[N:12]2[N:13]=1)=[O:27])[CH3:24]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 68838648HCID 68838648, compound

Product 1

HCID 68837068HCID 68837068, compound

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the product of Step 1 (0.23 g, 0.787 mmol), ethyl isocyanate (0.28 g, 3.93 mmol) and a catalytic quantity of dibutyltin diacetate (3 drops) in THF/toluene (1:1, 10 mL) was heated in a sealed tube at 100° C. for 15 h. This mixture was cooled to 0° C., the solid obtained was filtered and washed with 10% CHCl3/hexanes to provide the target compound, N-ethyl-N′-[5-(2-methyl-1,3-oxazol-5-yl)-7-pyridin-3-yl[1,2,4]triazolo[1,5-a]pyridin-2-yl]urea as a solid. LCMS (APCI+) 364.

Workup

  1. customthe solid obtained
  2. filtrationwas filtered
  3. washwashed with 10% CHCl3/hexanes

Sources & evidence

ORD record
ord-6b851651c4054ee4b52dbdd00e6f2f97
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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